


Late for a Date

by gemini28



Category: Problem Sleuth (Webcomic)
Genre: Crossdressing, M/M
Language: English
Status: Completed
Published: 2015-06-29
Updated: 2015-06-29
Packaged: 2018-04-06 18:39:26
Rating: Explicit
Warnings: No Archive Warnings Apply
Chapters: 1
Words: 3,055
Publisher: archiveofourown.org
Story URL: https://archiveofourown.org/works/4232577
Author URL: https://archiveofourown.org/users/gemini28/pseuds/gemini28
Summary: <blockquote class="userstuff">
              <p>Pickle Inspector is, once again, extremely late for a date with Droog. Or maybe he's right on time?</p>
            </blockquote>





	Late for a Date

**Author's Note:**

> This is just, so supremely self indulgent. Oh well

Pickle Inspector is running late. Or, at least, he thinks he is. There’s a six written on the back of his hand that he dimly remembers getting last night at some point, and he hadn’t noticed it was there until the clock said six-thirty. It’s a relief that he can at least remember that it’s a dinner date with Droog that he’s late for, because he doesn’t have to stop anywhere else, instead heading straight for Droog’s apartment. That’s always where they meet up before heading out, after all.

The front door is unlocked, surprising Inspector, but he figures that Droog must be expecting him and simply left it open for convenience’s sake. He hurries inside, through the entrance hallway, but all apologies he was building up in him die on his lips when he steps into the living room to find a distinct lack of Droog. Normally, the mobster would be lounging on the couch, reading his newspaper, or perhaps checking his watch obviously.

But he just…wasn’t there.

For a moment, Inspector wrung his hands, not totally sure how to deal with this sudden change in what he thought of as a normal routine. But thankfully, he didn’t have to stay there for very long, as the answer presented itself rather quickly. If Droog wasn’t in one place of the house, and they were set to meet up, obviously he’d be in another place! The simplicity of it is honestly relieving, and he starts walking, on autopilot really.

A quick look into the kitchen and Droog’s study (also uncharacteristically unlocked) comes up empty on the Droog front. Inspector is chewing at his lip by the time that he walks up to Droog’s bedroom door. Normally, Droog isn’t in here when they have a meeting set up, unless something’s wrong or there’s a sudden need for privacy. It can’t be the latter, though, because the door’s ajar. Inspector feels his nerves coil snakelike in his stomach, and is a bit dismayed at the way his hand shakes when he reaches for the doorknob.

All of the doors in Droog’s house open on silent hinges. Inspector has often wondered at the diligence shown in keeping everything so well oiled, but would put his guess on Droog simply wanting to keep an element of surprise on intruders.

Inspector’s words fail him for the second time in less than ten minutes, a fact he would be concerned about later once he thought it over. Sitting on Droog’s bed, peering into a mirror that Inspector knows from experience is difficult to look into and get a clear view of the door, is not Droog. It is not anyone he recognizes, actually. They’re wearing a long red dress, and those are certainly diamonds around their throat, but he’s unable to see their face. Without that crucial bit of information, he’s out at sea as to who the stranger could be.

This is unprecedented. Droog knows full well how Inspector deals with new people he isn’t prepared to meet, and doesn’t make a habit of having strangers over, usually. This person being here makes very little sense to Inspector, and he’s struck immobile with indecision. If he tries to leave, the person might see him and things will become awkward. If he stays in the doorway however, the person will absolutely see him and things will become awkward.

Inspector was so wrapped up in his important decision that he didn’t even notice when the stranger started to turn around, nor was he particularly aware of the little jump from them.

“Inspector?” A very familiar voice spoke up, and Inspector’s head snapped up, looking around for the source. The only person who could have spoken and been heard so clearly…was the one currently staring at him with a raised eyebrow.

Now that he could see their face full on, Inspector had absolutely no trouble whatsoever recognizing the stranger. It was Droog, looking just as surprised as Inspector surely felt. There’s a beat of silence, before he stands, and Inspector has to admire his silent grace even in a dress- GPI only knows Inspector himself would probably fall if he so much as wore such an elegant item of clothing.

“Inspector. I hadn’t been expecting you, as you likely can figure out.” He walks over, and the clicking sound on the polished wood floor tells Inspector that Droog’s wearing heels under that gown. Goodness, he really has gone all out, hasn’t he? “What are you doing here?”

There’s a moment where Inspector simply can’t get the words out in the right order. He clamps his mouth shut before he ends up embarrassing himself, or worse, and waits until he knows exactly what he’s going to say. He holds up the hand with the six written on it, nodding at it.

“W-We, ah. We had made plans… Right? I-I’m terribly sorry if I’ve gotten the date wrong, but I’m absolutely certain that I’ve gotten the time right!” He says, not even beginning to consider that Droog may have forgotten this time. Droog has never been late, he’s almost convinced the other man has some sort of inner scheduling mechanism from how punctual he is.

Droog steps forward and takes his hand in his own, before sighing heavily.

“Inspector, I wrote this, not you. Which means,” He taps his hand. “You read it upside down. We had arranged to meet up at nine o’clock, not six.” Inspector feels his cheeks heat up, and when he thinks about it, he can certainly remember Droog writing on the back of his hand. Oh, oh no. How incredibly embarrassing…

“I- I’m so sorry, I have no idea how I made such a mistake, I-" He wrings his hands and chews on his lower lip. “I’m sorry Droog, I didn’t mean to intrude on your, um, your personal time.”

“It’s quite alright. If nothing else, this is the earliest you’ve ever turned up for one of our meetings. I’ll consider it an even break.” Inspector only realizes that Droog’s been slowly backing him up against the wall when he bumps into it with a little jump.

“Y-Yes, well. Well, I should be….going now, shouldn’t I? I mean, I’ve clearly interrupted something, I wouldn’t want to be a bother-" He’s cut off from talking when Droog presses close to him, and as always Inspector is amazed that he can feel so small when being looked at by someone a fair bit shorter than him.

“Oh, no. That simply wouldn’t do. You’re here now, after all, and I can’t imagine that you’ll be as on time later when it actually counts. I should take advantage of this opportunity, don’t you think?” Droog sets a hand on his chest, and he really takes in what the gangster looks like. The dress, a really lovely deep red, suits him just as well as every other item of clothing he wears does.  Now that he can see Droog’s face up close he’s obviously got makeup on, the red on his lips being particularly enticing.

“I, uh.” Droog puts his hand on Inspector’s chest, and he worries at his lip. “Yes?”

The moment the word leaves his lips Droog is kissing him. His hands are on the Inspector’s waist, and they’re already trailing down. Inspector has no idea where to put his own hands for a moment, because that really is a beautiful dress and he doesn’t want to accidentally ruin it but on the other hand they are kind of going into having sex with it still on?

He puts his hands on Droog’s shoulders, and is immediately thankful for this decision as Droog sucks a hickey onto his neck and his knees go weak. He gasps, and the thought of that red lipstick ringing the mark makes him groan in the back of his throat.

One of Droog’s hands has made its way down to Inspector’s crotch, lightly squeezing. He couldn’t help but to make an embarrassed whine at how outrageously hard he was already. He wasn’t sure if it was the dress, or just Droog in general, but he knew that whatever was causing his blood to race like this, he wanted it to continue.

“My, my, Inspector.” Droog’s voice is a low purr that goes right through Inspector. He’s always had something of a weakness for Droog’s voice… “I wonder, what is it about all this that’s getting you most excited? Is it the dress, perhaps? Or are you always this…responsive, and I’ve simply never noticed?”

There’s barely a smirk on his face at Inspector’s flustered stumbling over his words, and he kisses him again before he can even get a word out. Then Droog’s trailing the kisses down, and he’s…getting down onto his knees? This isn’t exactly unheard of, but in such a lovely dress (and heels to boot), it takes Inspector by some surprise. Though he certainly is not complaining, not by a long shot. 

Droog undoes his pants and pulls them down in one swift, easy motion, glancing up and smirking at the shade of red Inspector’s cheeks have become. Inspector tries and tries to keep his cool in situations like this, but Droog’s own cultivated calmness always manages to make him more flustered than almost anything else.

Then there’s lips wrapped around his dick, and it’s a lot more than just Droog’s personality that’s making him go weak-kneed. He moans, and reaches up to cover his mouth, but is surprised when Droog stops him halfway there and pins his arms against the wall.

“I much prefer to hear you, Inspector. Don’t be shy.” Said with the same amused tones that he says almost everything with. Inspector chews on his lip for a second, before settling his hands on Droog’s shoulders instead of fussing with his outfit and ruining it. That gets him an approving look, and he can’t stop his smile.

Inspector is always surprised at how good Droog is at blowjobs. He really wouldn’t have taken the other man for someone who has a dick in his mouth enough to get good at it. He would have guessed it being the other way around, before they’d gotten involved. But Droog has no trouble at all going down on him, and in no time his expert working over has Inspector moaning loudly and clinging onto him for dear life.

It’s feeling good, and Inspector is starting to feel short of breath, when Droog pulls away. Inspector can’t help the whine he makes, even though it’s embarrassing to complain when he probably should have guessed that Droog wouldn’t just blow him and be done with it.

“Oh, don’t complain. I’d hardly leave you hanging.” He says, running his thumb over his dick just to see him squirm. “Well, not tonight, anyhow.” Inspector swallows thickly and glances down, only to see that Droog left behind extremely deliberate lipstick marks all down his dick.

Droog’s lipstick isn’t smeared, though, when he gets up to kiss Inspector again, and he kind of marvels a little at this fact. He wonders at what kind of magic Droog uses to continue to look flawless even after sucking dick.

He can’t continue on that train of thought for too long, though, because Droog’s hands are sliding themselves down to grope at him and, _oh._ Droog’s picked him up right off the ground, his hands holding tight onto his thighs. Inspector knows that it’s not too difficult to pick him up anyhow, but he’s always pretty impressed that people can actually hold him once they’ve got him up. Just another thing that he can admire about Droog (which he does happily, the dress has no sleeves).

They go back to kissing, and Inspector nearly allows himself to just drift off into delight of everything, but something occurs to him just as Droog presses closer.

“Ah- Wait! I, uh. I don’t have anything on me, do…you?” He glances over the dress. It’s lovely, but there aren’t any pockets that he can see. Droog just raises an eyebrow at him and holds up a tube that Inspector honestly hadn’t even seen him take out of…wherever. Inspector stares for a moment, before huffing. “Well…Alright, you’ve got me there. No complaints then, I suppose...”

He hears Droog chuckle and tries not to look too embarrassed about things. This is made harder by the sound of a cap popping, and Droog shifting Inspector so that he only has to balance him with one hand. Inspector helps him along by wrapping his legs around his waist, trying very hard not to just grind right up against the dress. His arms go a little tighter around his neck, because the last thing he wants is to be dropped.

He shifts a little, almost uncomfortable, when Droog starts pressing fingers inside of him. They’ve done this plenty of times, of course, but he’s never quite gotten used to this first part. Droog leans in and bites softly at his neck, far too high to hide easily, and even though his breathing quickens Inspector manages to relax.

Droog knows Inspector well enough to be able to play him as well as he plays his saxophone. He’s able to move his fingers just so, and Inspector moans loudly into his ear, bucking his hips down as far as he can and coming dangerously close to falling down. Droog keeps a tight grip on him, though, for which he is eternally grateful.

Droog takes out his fingers before long, and pulls a handkerchief out from nowhere again, and wipes his hands clean. Inspector can’t help but to look at him with excitement, leaning into the wall a bit. Droog is handsome when he’s concentrating, and Inspector is so caught up in him that he is taken by some surprise when Droog starts to push into him.

There’s a hand around his dick again as Droog pushes in slowly, and he squirms under all the attention. Droog’s returned to sucking marks on his neck, and groans once he’s in to the hilt. Inspector makes an odd, high kind of noise, the kind he only makes when he’s particularly overwhelmed by a certain angle.

It gets louder when Droog starts to move and starts stroking Inspector slowly. If he wasn’t so worried about falling, he would move his hands to cover his face. He simply can’t handle the look that Droog gives him when he starts really being loud. It makes his breath catch in his throat, and his stomach get all twisty. And that’s in addition to what sex itself does to him.

Droog braces himself up against the wall, and Inspector moans when his pace quickens. He feels glad that they’re not fucking up against a wall that Droog shares with a neighbor, or else that would make this all especially embarrassing. As it is, though, he just cries out and digs his fingers into Droog’s shoulders. They’re the only thing he can hold onto, right now, that won’t muss up any of Droog’s carefully cultivated look.

Droog knows just how to work him over, and eventually Inspector is moving his hips frantically, his gasping breaths coming in short bursts as he gets closer and closer. It only takes a few more tugs and the soft breathing of his name into his ear for him to come, loud and whining.

Droog’s hips stall, and he takes in a sharp breath. Inspector barely even notices, still riding the high of his orgasm, but he does whine a little when Droog starts moving again. It’s almost on the edge of being over stimulating, but it doesn’t cross that line, and he is relieved when Droog grips onto his hips hard and comes with an almost-growl.

Inspector allows himself to just kind of be moved around, but when he’s let down onto his feet his legs almost immediately give out and he just sort of….slides down the wall  and onto the floor. He closes his eyes and sighs, only opening them once Droog’s crouched down next to him.

“We have three hours to pass before dinner time. Would you be interested in working up an appetite, for once?” He says it as a question, but Inspector wonders. He considers the pros and cons of agreeing before, tentatively, nodding his head. Droog’s expression turns into a smile, and he feels just a bit excited. “Wonderful. I just knew you’d be interested.”

* * *

 

Sometime later, Inspector is woken up by someone shaking his shoulder. He almost doesn’t wake up, but the shaking doesn’t stop, and when he opens his eyes he’s sitting straight up in the bed he fell asleep in. Droog is standing there, looking expectant, and is dressed far differently than he’d been earlier. He’s got a suit on this time, and no trace of makeup to speak of.

“Come on, get up. Get dressed, and we’re leaving.” He nods at the clock next to the bed, and Inspector eyes it warily, like it’s a doomsday clock. Still, he makes himself stand up and stretch, and retrieve his (folded, ironed) clothes from the nearby chair. He glances over at Droog, who is waiting by the door, and looks curious.

“You’re, um, not going to be wearing the dress?” Does he sound hopeful? Surely not, no. Still…He is a bit confused and interested as to why Droog would bother to get all dressed up one way, only to actually go out in another whole outfit. It seems like an awful lot of trouble to go through, in Inspector’s opinion.

“No.” Simple, to the point, and unfortunately expected. But what he doesn’t expect is for Droog to actually continue. “I prefer to keep that facet of my interests separate from others. Especially when a restaurant has a reservation under my name.”

“O-Oh. That makes sense, yes…” Inspector says as he tugs on his sweatervest again. He is beyond glad that he got a nap in before they had to leave. He’s pretty sure that after all…that, asking him to function in a public setting would be asking too much. He straightens up and walks over to Droog, taking the offered arm happily.

He follows him out of the apartment, and makes a mental note to be early for dates more often. 


End file.
